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Sodium Iodide → 7-(4-(4-(2-ethoxyphenyl)-1,4-diazepan-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one

HRID 1750099
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HRID 1750099 반응식
Cl[C:2]1[C:7](Cl)=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:15][CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:30]=[C:29]3[C:24]([CH:25]=[CH:26][C:27](=[O:31])[NH:28]3)=[CH:23][CH:22]=2)[CH2:11][CH2:10]1.[Na+].[I-].Cl.[CH2:35]([O:37]C1C=CC=CC=1N1CCCNCC1)[CH3:36].C([O-])([O-])=O.[K+].[K+]>CC#N.O>[CH2:35]([O:37][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:15][CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:30]=[C:29]3[C:24]([CH2:25][CH2:26][C:27](=[O:31])[NH:28]3)=[CH:23][CH:22]=2)[CH2:11][CH2:10]1)[CH3:36]
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참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 665595887-(4-(4-(2,3-dichlorophenyl)-1,4-diazepan-1-yl)butoxy)quinolin-2(1H)-oneHCID 666337571-(2-Ethoxyphenyl)-1,4-diazepane hydrochloride

생성물 1

HCID 565988787-(4-(4-(2-ethoxyphenyl)-1,4-diazepan-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one수율 44%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A mixture of intermediate 4 (150 mg, 0.5 mmol) and NaI (150 mg, 1.0 mmol) in CH3CN was heated to reflux for 30 min and then cooled to rt. Intermediate 31 (129 mg, 0.5 mmol) and anhydrous K2CO3 (276 mg, 2.0 mmol) were then added to the mixture. The resulting mixture was heated to reflux and stirred overnight. The reaction solution was diluted with water and extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with DCM/MeOH=50:1) to give 7-(4-(4-(2-ethoxyphenyl)-1,4-diazepan-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one (compound 12) (95 mg, 44%). 1H NMR (300 MHz, CDCl3) δ 7.75 (bs, 1H), 7.04 (d, J=8.1 Hz, 1H), 6.92-6.83 (m, 4H), 6.52 (dd, J=8.4 Hz, 2.1 Hz, 1H), 6.30 (d, J=2.7 Hz, 1H), 4.04 (q, J=6.9 Hz, 2H), 3.96-3.94 (m, 2H), 3.38-3.29 (m, 4H), 3.02-2.93 (m, 4H), 2.89 (t, J=6.9 Hz, 2H), 2.74-2.70 (m, 2H), 2.61 (t, J=8.1 Hz, 2H), 2.14-2.10 (m, 2H), 1.83-1.79 (m, 4H), 1.45 (t, J=6.9 Hz, 3H). HPLC: 99%, RT 2.438 min. MS (ESI) m/z 438.2 [M+H]+.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 30 min
  3. temperatureThe resulting mixture was heated
  4. temperatureto reflux
  5. extractionextracted with EtOAc
  6. washThe combined EtOAc layers were washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo
  9. custompurified by flash chromatography on silica gel column (elution with DCM/MeOH=50:1)

출처 및 근거

ORD 기록
ord-fcd178820b754556af572c3380323a25
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09156822B2

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